hydrogenchloride in acetone T=20°C; 4 h;

1.1: n-BuLi / diethyl ether; hexane / 0.17 h / -30 °C 1.2: 80 percent / tetrahydrofuran; diethyl ether; hexane / 2 h / 20 °C 2.1: 97 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; POCl3 / pyridine / 20 - 80 °C 3.1: H2 / Pd/C / methanol; tetrahydrofuran / 20 h 4.1: conc. sulfuric acid / tetrahydrofuran; H2O / 1.5 h View Scheme

1: H2 / Pd/C / methanol; tetrahydrofuran / 20 h 2: conc. sulfuric acid / tetrahydrofuran; H2O / 1.5 h View Scheme

1.1: 90 percent / N-bromosuccinimide / CHCl3 / 3.5 h / Heating 2.1: n-BuLi / diethyl ether; hexane / 0.17 h / -30 °C 2.2: 80 percent / tetrahydrofuran; diethyl ether; hexane / 2 h / 20 °C 3.1: 97 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; POCl3 / pyridine / 20 - 80 °C 4.1: H2 / Pd/C / methanol; tetrahydrofuran / 20 h 5.1: conc. sulfuric acid / tetrahydrofuran; H2O / 1.5 h View Scheme

1: 97 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; POCl3 / pyridine / 20 - 80 °C 2: H2 / Pd/C / methanol; tetrahydrofuran / 20 h 3: conc. sulfuric acid / tetrahydrofuran; H2O / 1.5 h View Scheme

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 24 h / 100 °C / Inert atmosphere 2: 5 Pd(II)/C(eggshell); hydrogen / methanol / 2 h / 20 °C / 2068.65 Torr 3: hydrogenchloride / acetone / 4 h / 20 °C View Scheme